Triethylamine → HCID 20773299, compound

HRID 1814804Notes

Reaction equation

HRID 1814804 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][N:3]1[C:9](=[O:17])[C@:10]([OH:16])([CH3:15])[C:11]([F:14])([F:13])[F:12].C(N(CC)CC)C.[C:25]([C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1)#[N:26]>CCOC(C)=O>[CH3:1][C@H:2]1[CH2:7][N:6]([S:33]([C:30]2[CH:29]=[CH:28][C:27]([C:25]#[N:26])=[CH:32][CH:31]=2)(=[O:35])=[O:34])[C@H:5]([CH3:8])[CH2:4][N:3]1[C:9](=[O:17])[C@:10]([OH:16])([CH3:15])[C:11]([F:14])([F:12])[F:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 10587022HCID 10587022, compound

Product 1

HCID 20773299HCID 20773299, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of (R)-[(2S,5R)-2-methyl-5-methyl-1-(3,3,3-trifluoro-2-hydroxy-2-methylpropionyl)piperazine] (J. Med. Chem., 1999, 42, 2741-2746] (254 mg, 1.0 mmol) and triethylamine (0.17 ml, 1.2 mmol) in EtOAc (15 ml) was added a solution of 4-cyanobenzene sulphonyl chloride (220 mg, 1.1 mmol) in EtOAc (10 ml). The resultant mixture was stirred at ambient temperature for 2 hours, washed with 1 M hydrochloric acid, saturated sodium hydrogen carbonate solution and brine, dried and evaporated. The residue was recrystallized from EtOAc/hexane to give the title compound as a solid (280 mg, 0.56 mmol). Mp: 186-187° C.; NMR: 0.95 (d, 3H), 1.25 (d, 3H), 1.75 (s, 3H), 3.25 (dd, 1H), 3.35 (d, 1H), 3.5 (dd, 1H), 4.2 (m, 3H), 4.75 (s, 1H), 7.8 (d, 2H), 7.9 (d, 2H); m/z 418.

Workup

  1. washwashed with 1 M hydrochloric acid, saturated sodium hydrogen carbonate solution and brine
  2. customdried
  3. customevaporated
  4. customThe residue was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-bd7c389e91584e5295374165c8161df9
Source dataset
uspto-grants-2005_04
Patent number
US06878712B1

Reaction notes

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